Similar to Route 1 in Kanto, Trainers traveling from Cherrygrove to New Bark can hop over a series of ledges to avoid the grassy areas and to travel between the two areas quickly while Trainers traveling from New Bark to Cherrygrove must travel through a series of grass patches to reach their destination. The first such patch is near the start of the route where the path turns south into the patch to circumvent a ledge. Route 29 westbound continues to follow the ledge south, then to the west before the route opens up at a T-intersection. To the west, Trainers whose Pokémon can use Cut outside of battle can chop down a tree to open a grass-less path to Cherrygrove. Those who do not have Cut, however, must go north through a break in the ledge.
In this location on Tuesdays after Falkner, the Violet City Gym Leader, has been defeated, Tuscany, one of the Week Siblings, appears, giving any Trainers that talk with her a Pink Bow, (a TwistedSpoon in Generation IV) the first time the player meets her, and a Shock Ribbon the second time and afterwards (Generation IV only). Immediately north of Tuscany, there is another tree that can be cut to avoid two grass patches to the northeast. However, Trainers lacking Cut are forced to traverse either of the two patches. Regardless of which way a Trainer takes, the route curves to the west, merging with the second Cut shortcut path directly south of a gate which separates Route 29 from Route 46 in the north. Between this and Cherrygrove City is your first encounter with your rival.
East of the gate, the path heads to the northwest, then to the southeast, passing through another grassy area before straightening out and traveling due west. The route then juts south, merging with the first Cut shortcut path as it turns to the west, then north and west again as it enters Cherrygrove.
Route 29 is in a mountainous region of Johto, which means that the Headbutt-able trees that line the route hold Pokémon often found in the mountains, namely Spearow and Aipom. The route is also home to the Dude, who teaches players how to capture Pokémon (and also turns the player away from the route if the player doesn't have a Pokémon). In HeartGold and SoulSilver, this duty was given to Lyra or Ethan (depending on the player character's chosen gender).